3-Bromo-1,1,1-trifluoro-2-propanone → 5-[1-[4-(methylsulfonyl)phenyl]-4-hydroxy-4-(trifluoromethyl)-4,5-dihydro-1H-imidazol-2-yl)-1,3-benzodioxole

HRID 1352943

반응식

HRID 1352943 반응식
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([C:10](=[NH:22])[NH:11][C:12]3[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=3)=[CH:4][C:3]=2[O:2]1.C(=O)(O)[O-].[Na+].Br[CH2:29][C:30](=[O:35])[C:31]([F:34])([F:33])[F:32]>C(O)(C)C>[CH3:21][S:18]([C:15]1[CH:14]=[CH:13][C:12]([N:11]2[CH2:29][C:30]([OH:35])([C:31]([F:34])([F:33])[F:32])[N:22]=[C:10]2[C:5]2[CH:6]=[CH:7][C:8]3[O:9][CH2:1][O:2][C:3]=3[CH:4]=2)=[CH:17][CH:16]=1)(=[O:19])=[O:20]

참가 물질

5

반응물 3

HCID 790083-Bromo-1,1,1-trifluoro-2-propanoneHCID 516892Sodium BicarbonateHCID 178504792HCID 178504792, 화합물

생성물 1

HCID 105986165-[1-[4-(methylsulfonyl)phenyl]-4-hydroxy-4-(trifluoromethyl)-4,5-dihydro-1H-imidazol-2-yl)-1,3-benzodioxole수율 47%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

To a mixture of 3,4-methylenedioxy-N-[4-(methylsulfonyl)phenyl]benzenecarboximidamide from Step 1 (2.32 g, 7.3 mmol) and sodium bicarbonate (1.23 g, 14.6 mmol) in isopropanol (100 mL), 3-bromo-1,1,1-trifluoroacetone (5.4 mL, 52 mmol) was added. After heating the reaction mixture to reflux for 24 hours, the solvent was removed. The residue was redissolved in methylene chloride and washed with water. The organic fractions were combined, dried over sodium sulfate, filtered and concentrated in vacuo. The crude mixture (7.1 g) was purified by chromatography (silica gel, toluene/ethyl acetate, 1/1) to give 5-[1-[4-(methylsulfonyl)phenyl]-4-hydroxy-4-(trifluoromethyl)-4,5-dihydro-1H-imidazol-2-yl)-1,3-benzodioxole (1.46 g, 47%) as a white solid: mp 200–202° C. Anal. Calc'd. for C18H15N2SO5F3.0.25 PhCH3: C, 52.55; H, 3.80; N, 6.21. Found: C, 52.73; H, 3.78; N, 6.01.

후처리

  1. additionwas added
  2. temperatureAfter heating the reaction mixture
  3. temperatureto reflux for 24 hours
  4. customthe solvent was removed
  5. dissolutionThe residue was redissolved in methylene chloride
  6. washwashed with water
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude mixture (7.1 g) was purified by chromatography (silica gel, toluene/ethyl acetate, 1/1)

출처 및 근거

ORD 기록
ord-1aa56be41c6a44b3bf92a7376da33a45
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07220770B2

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